How to Transfer From Midway to O’Hare Airport in Chicago

Wow… six posts later, I’ve finally finished writing about the holiday trip I took with Matt! Hard to believe that we set off for our travels almost 3 months ago already. Anyway, it’s time for some new topics!

Last week, my mom and I visited Sevilla in the south of Spain. I was able to find her a relatively cheap flight to Madrid to spend a week with me here. And if you didn’t know it already, I booked a last-minute flight home to Kansas City to watch the Super Bowl with my family (just for a weekend). Which was also super cheap. But how did I do it?

Well, as a rule, flying between Kansas City and anywhere else in the world is generally pretty expensive. There just aren’t direct flights from KC to Europe, or Asia, or anywhere international except maybe Mexico and Canada. So at some point, I realized it was cheaper to book a direct flight from Chicago to Madrid.

Using the Southwest Airlines points I racked up in my former life as a traveling technology consultant, I can get myself between KC and Chicago pretty easily. By booking my subsequent international flight directly in/out of Chicago, it can save hundreds of dollars off the overall cost of my trip.

Depending on your situation and where you live, you might also find it more cost-effective to fly to Chicago with Southwest Airlines and then transfer to your international flight. But here’s the only problem: Chicago has TWO airports. And the one that Southwest flies into – Midway – is not the one that international flights depart out of.

Of course, you can always Uber or take a taxi between the airports. But this can be expensive, and depending on traffic, it might not be your fastest option either. And you should know by now: I love taking public transportation. So here, I’m going to explain to you exactly how to transfer between Chicago-Midway and Chicago-O’Hare airports using the CTA (Chicago Transit Authority) Trains.

First Things First

If you’re planning to do this, there are a couple of important things to keep in mind. Most importantly, since you’ve got two separate tickets (Southwest + International Flight), these airlines will not communicate with each other in case of delay. And this means they aren’t going to have any sympathy for you if something goes wrong such as a delay or missed connection. For that reason, I recommend booking tickets with PLENTY of time in between to connect. The average travel time between Midway and O’Hare is 90 minutes.

I’d recommend a minimum of 4 hours between your arrival time to one airport and departure time from the other airport. Remember that you’ll have to go through customs/immigration, find the train, take the train, connect in the city (more on that later), potentially shuttle between terminals, go to the check-in desk, go through security again, etc.

Also, make sure to download my favorite travel app ever, Citymapper! (No, they aren’t paying me for how much I promote them. I just love them that much.) It really helps to follow along on the journey.

Midway to O’Hare Instructions

After arriving at Midway on Southwest Airlines

1. Follow all signs to exit the terminals (but stay inside).

2. Follow all signs that say “CTA Trains” or “Trains to City.” 5-10 minute walk.

3. Upon reaching CTA station, buy a ticket (Ventra Card) from the vending machine. Buy the “Single Ticket” which costs $3. Pay with cash or card.

4. Go through the ticket turnstiles and down the escalators to the trains. You’re taking the Orange Line which is the only line at this airport. Get on the next train and ride it toward the city center. 20-25 minutes.

5. Get off the train at station Clark/Lake. This is where you have to change, but the Orange Line is elevated and the Blue Line (which you need to go to) is the subway.

6. Go down the stairs from the elevated platform and follow the signs for the Blue Line. You shouldn’t need it, but in case you get confused and accidentally exit the station (or you stop somewhere downtown for food) your Ventra Card you bought at Midway will still work. So you can exit and re-enter the station using the same ticket.

7. Follow the signs for the Blue Line towards O’Hare Airport. Get on the next train and ride it to the last stop. 40-50 minutes.

8. After arriving, follow the signs to whichever terminal you’re flying out of. *Even if it’s an international flight, you might not fly out of the International Terminal.

*8.5. If you ARE flying out of the International Terminal (T5) you will have to follow the signs to Terminal 2 and take the shuttle to Terminal 5.

9. Check in at your airline’s ticket desk and proceed through security.

O’Hare to Midway Instructions

After arriving at O’Hare from your international flight

1. It’s likely that you will arrive in Terminal 5, but you need to go to Terminal 2 to get the CTA train. Follow the signs for shuttles or just ask one of the workers. The shuttle is FREE.

2. After arriving in Terminal 2, follow all the signs that say “CTA Trains” or “Trains to City.”

3. Upon reaching CTA station, buy a ticket (Ventra Card) from the vending machine. Buy the “Single Ticket” which costs $5. Pay with cash or card.

4. Go through the ticket turnstiles and down the escalators to the trains. You’re taking the Blue Line which is the only line at this airport. Get on the next train and ride it toward the city center (direction Forest Park). 40-50 minutes.

5. Get off the train at station Clark/Lake. This is where you have to change, but the Blue Line is the subway and the Orange Line (which you need to go to) is elevated.

6. Go up the stairs from the subway, following the signs for the Orange Line. You shouldn’t need it, but in case you get confused and accidentally exit the station (or you stop somewhere downtown for food) your Ventra Card you bought at O’Hare will still work. So you can exit and re-enter the station using the same ticket.

7. Follow the signs for the Orange Line towards Midway Airport. Get on the next train and ride it to the last stop. 20-25 minutes.

8. After arriving, follow the signs to the terminal (there’s only one). No need to check in at the desk unless you want to, because you can download your boarding pass on your phone, so you can just go through security.

 

So, there you have it! The step-by step instructions of transferring from Midway to O’Hare, or the other way around, in Chicago.

Is there anything else you want to know about the process? Have you ever done it before? Leave me a comment!

-Cathy

Originally Published on March 11, 2020.